


The Valentines Day I Dressed up for My Boyfriend

by littlefirefly31



Series: Kink/Request Fics [54]
Category: Supernatural RPF
Genre: Crossdressing, Jensen in Panties, M/M, Panties, bottom!Jensen
Language: English
Status: Completed
Published: 2014-12-26
Updated: 2014-12-26
Packaged: 2018-03-03 15:33:20
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,412
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2856002
Author URL: https://archiveofourown.org/users/littlefirefly31/pseuds/littlefirefly31
Summary: <blockquote class="userstuff">
              <p>Prompt: I read [The Halloween I Lost My Virginity] awhile back. Would love to read more on young J&J's life as it pertains here in this Fan Fiction! Very Hot! I Love that you gave Jen an "Excuse" to cross dress. I would Love it if there were more Fan Fiction on that subject. Either one would make a beautiful woman!</p>
            </blockquote>





	The Valentines Day I Dressed up for My Boyfriend

**Author's Note:**

> This is sort of a timestamp to The Halloween I Lost My Virginity, because it follows the same plotline, but it can be read on its own without real confusion.

**Prompt** : I read [The Halloween I Lost My Virginity] awhile back. Would love to read more on young J&J's life as it pertains here in this Fan Fiction! Very Hot! I Love that you gave Jen an "Excuse" to cross dress. I would Love it if there were more Fan Fiction on that subject. Either one would make a beautiful woman!

 

Jensen thought his boyfriend was freaking adorable. Even after three and a half months of dating, Jared blushed and stuttered whenever Jensen winked at him in the hallway. It was such a change from the bedroom, where Jared held Jensen down and fucked him fiercely. The juxtaposition only made Jensen want him more.

And now Valentines Day was coming up. Jensen wanted to do something special for Jared, something unique. He was brainstorming while getting dressed, and then his fingers brushed across something silky soft. The lacey pink underwear Danneel bought him on Halloween were laying innocently at the top of the drawer next to the garter belt. He smirked. Jensen remembered how crazy the panties drove Jared at Halloween. He could put on some makeup, maybe borrow Danneel’s skirt, and give Jared a really happy Valentines Day.

Danneel was very much willing to lend Jensen some clothes and makeup, begging for photos. “No way. The information about my and Jared’s sex life is only available to two people.”

“Sophia and me?” Danneel suggested hopefully.

“Jared and _me_ ,” Jensen corrected.

“I can ask Jared.”  
Jensen snorted. “If you try talking about sex with that kid he’ll blush and stammer out some excuse. It’s adorable.”   
“You softie.” Danneel handed him a short little skirt and a matching top. “Want a bra?”  
“Nah, the panties are good enough for me.” Jensen paused. “What a weird sentence.”

Danneel laughed. “Go woo your boyfriend, sexy.”

*

Jensen invited Jared over at 9. His parents would be out having a Valentines dinner of their own, so Jensen could be as loud as he wanted when Jared fucked him. The thought made his cock plump up in his panties. God they were soft. Girls totally had it lucky when it came to underwear.

He hadn’t perfected putting on makeup yet, so he stabbed himself in the eye a couple times trying to put on eyeshadow. At least he didn’t have to pick out the right colors; Danneel had done everything for him. He may have got a little heavy with the blue, but it looked alright to him. He was finishing up the lip-gloss when the doorbell rang.

Jensen adjusted his skirt the last time and left his room. “Door’s open!” He yelled.

Jensen heard the click and then Jared’s soft shuffle. “Where are you?”

“Upstairs, baby,” Jensen told him. “C’mon, I wanna give you your present.”

The sound of feet jogging up stairs echoed in the empty house. Jensen slid back into his room and lay down on his bed. He wondered what Jared’s reaction would be. God, he’d love it if his boyfriend just went crazy and fucked him right there. He wouldn’t even prep Jensen that much, just enough to get his dick in. Jensen wanted to feel Jared for the next week or more. He dabbed at his lip-gloss one last time and then relaxed.

“Why’d you wait up here—oh my god, Jensen, what do you have _on_?”

Jensen smirked at him. “I figured I shouldn’t let such a nice outfit go to waste.”

Jared crawled on the bed beside him and ran his hand down Jensen’s leg. “Wow, Jensen…”

“Call me Jenny,” Jensen replied. “Seems appropriate.”

Jared leaned over his boyfriend. “You look beautiful.”

“I spent a while on my makeup,” Jensen winked. “Does it look good?”

“Christ, you look amazing.” Jared slid a hand underneath Jensen’s skirt until he reached his panties. “God, I’m so hard right now.” His hand helped ease the shirt off Jensen and then he licked across a nipple. “Flowers and chocolates weren’t enough for you?”

“Oh baby, I go all out.” Jensen ran his hand through Jared’s soft hair. “Now come on, cowboy. I didn’t get all dolled up for you to just stare at me.”

Jared snorted. “But didn’t you? You love when people stare at you, including me.”

Jensen shrugged. He did love it. Jared’s eyes on him made him feel alive. Jared smiled and slid down his body to push the skirt up. He ran his fingers over the lace panties and Jensen’s hard dick. “We should get you bigger panties. These can hardly hold you.” He nuzzled Jensen’s crotch. “Bulging out of the lace… it’s obscene.”

Jensen’s breath came unevenly. “Don’t tease.”   
Jared bit the inside of Jensen’s thigh. “You wore panties. I’m allowed to tease.”

“You suck,” Jensen groaned.

“I might.” Jared pushed Jensen’s skirt up higher so his crotch was on full display. Jared ran his fingers across the panties and the garter belt. “Your body would make a preacher break his vows.”

Jensen spread his legs wider. “I didn’t dress up for me, sweetheart.”

“Oh, Jenny,” Jared purred. “You may have done this for me, but I know how you love the feeling of lace. I’m your boyfriend; I know all your kinks. Including your panty fetish.”

Jensen groaned. “That word sounds so sexy coming out of your mouth.”

His boyfriend leaned up and kissed him, smearing the lip-gloss between their lips. “Such a pretty girl,” Jared cooed. “My sweet, pretty Jenny.”

Jensen whined. “Oh god-,”

“I just want to kiss your pretty lips all night.” Jared leaned down and kissed the corner. “You taste like strawberries. Is it Danneel’s?” Jensen nodded. “Ask her if you can keep it. Makes your lips even more kissable.”

Jensen whined breathlessly when Jared’s hand went back to massaging Jensen’s cock. “Such a good girl, Jenny. You’re so sweet and lovely with those long eyelashes and pretty lips.”

Jensen wrapped an arm around Jared’s waist. “I need you. Please.”

“In good time, Jenny.” He slid his fingers underneath the pink waistband. “I want to take my time with my pretty girl.”

Jared’s tongue licked around the edge of the panties. The fabric dampened with his spit. The skirt brushed across Jared’s forehead. “Your eyes are so pretty. They look like a girl’s.”

“That was the idea,” Jensen sighed. Jared’s strong fingers massaged his thighs and ass. It felt really nice. “Hm, keep doing that.”

“Anything to keep my girl happy,” Jared purred.

Jensen flushed with pleasure. “I do kinda like the panties.”   
“Oh, I know.” Jared walked a hand up Jensen’s torso and then rolled a nipple between his fingers. “And I plan to buy you many more pairs, and some makeup, too. Maybe next time you’ll put on a dress for me and let me kiss the lip-gloss off you.”

Jensen’s dick was begging for attention, even more so with Jared’s words. “Tell me I’m pretty,” Jensen demanded.

Jared nuzzled his ear and sucked on a lobe. “You’re my pretty girl, my sweet little angel. So beautiful for me, Jenny.”

Jensen bucked his hips. “It hurts, Jay.”

“Okay, princess.” Jared finally peeled down Jensen’s lacy underwear and wrapped his mouth around his dick. Jensen moaned and his head fell back against his pillow. “Thank you, thank you!”

Jared licked and sucked Jensen’s dick while his hands pulled on Jensen’s nipples or fondled his balls. Jensen vibrated on the bed, letting out little noises. “Oh, oh, oh,” Jensen panted. “Jared! I’m gonna, I’m gonna-,”

Jared slid to the end of his dick and licked at the head, lapping at the precome. “Please,” Jensen sobbed.

Jared took him into his mouth, and too Jensen’s surprise and delight, Jared swallowed him up to the root. “You’ve been practicing.”   
Jared winked at him and focused on his task of bringing Jensen to orgasm. The fabric of the panties rubbed against his thighs and Jared’s coos of “pretty girl” pushed Jensen over the edge and his orgasm spurted into Jared’s mouth.

He swallowed Jensen’s come and then crawled up the bed to kiss Jensen. Jensen licked the taste out of Jared’s mouth. He was sleepy and pulled Jared onto the bed with him. “Dude.” He reached a hand down to jerk Jared off but found the front of his underwear wet. “Did you come?”

Jared blushed. “You’re in a skirt and lace panties, Jen. _Pink lace_. What was I supposed to do?”

Jensen kissed his boyfriend’s adorable nose. “Happy Valentines Day, Jared.”  
“Happy Valentines Day, Jenny.”


End file.
